Triethylamine → HCID 178418902, 화합물

HRID 7805

반응식

HRID 7805 반응식
[NH2:1][C:2]1[C:3]([OH:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C(N(CC)CC)C.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C.CO>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]([C:18]([F:17])([F:28])[F:29])=[CH:20][CH:21]=2)[C:3]([OH:9])=[N:4][CH:5]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 178418959HCID 178418959, 화합물

생성물 1

HCID 178418902HCID 178418902, 화합물수율 60%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a solution of 3-amino-5-bromopyridin-2-ol from Step C (1.5 g, 7.9 mol) and triethylamine (1.64 mL, 11.9 mol) in tetrahydrofuran (15.8 mL) at 0 C was added dropwise 4-trifluoromethylbenzoyl chloride (1.2 mL, 7.9 mol). The reaction mixture was stirred at 0° C. for 1 h and warmed to room temperature for 15 h. Potassium carbonate (1.64 g, 11.9 mol) and methanol (15.8 mL) were added and the reaction mixture was stirred at room temperature for 6 h. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated ammonium chloride solution and brine. The separated organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. Purification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes) gave 1.72 g (60%) of the title compound.

후처리

  1. temperaturewarmed to room temperature for 15 h
  2. stirringthe reaction mixture was stirred at room temperature for 6 h
  3. washwashed with saturated ammonium chloride solution and brine
  4. dry with materialThe separated organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-398716f2fe394a7f9a626f6e1dd67830
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087622B2

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